


Hitchhiking and Propositions

by halcyon1993



Series: The Kinky Adventures of a Wolf and His Boy [79]
Category: Teen Wolf (TV)
Genre: Age Difference, Alternate Universe - Human, Anal Fingering, Anal Sex, Barebacking, Bottom Stiles Stilinski, Daddy Kink, Dirty Talk, Dom/sub Undertones, Face-Fucking, First Meetings, Hopeful Ending, Humiliation, Loss of Virginity, M/M, Mildly Dubious Consent, Older Derek Hale, Oral Sex, Orphan Stiles Stilinski, Plot What Plot/Porn Without Plot, Rimming, Rough Sex, Scent Kink, Top Derek Hale
Language: English
Status: Completed
Published: 2020-09-16
Updated: 2020-09-16
Packaged: 2021-03-07 01:53:57
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 8,811
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26498944
Author URL: https://archiveofourown.org/users/halcyon1993/pseuds/halcyon1993
Summary: Stiles hitchhikes and gets picked up by an older man.
Relationships: Derek Hale/Stiles Stilinski
Series: The Kinky Adventures of a Wolf and His Boy [79]
Series URL: https://archiveofourown.org/series/887604
Comments: 36
Kudos: 768
Collections: Teen Wolf ▶ Derek Hale / Stiles Stilinski





	Hitchhiking and Propositions

**Author's Note:**

  * For [Lazydink](https://archiveofourown.org/users/Lazydink/gifts).



> As always, don't judge me for the depravity I have written. ;)

Stiles wipes sweat from his brow and laments the current state of his life.

It started when he was thirteen years old. He was happily living with his dad, the Sheriff of Beacon Hills, California. He only had one friend in Scott McCall, but Scott was the best friend he could've asked for. Then it all went to shit. Scott's mother, Melissa, got a job opportunity just outside of NYC that would see her earning a lot more money, money she could really use to pay for Scott's college education in a few years. So, of course, she took it and moved across the country, and she took Scott with her.

Stiles was friendless then, but at least he still had his dad. Until a year later, when he was fourteen and the Sheriff was killed in a robbery gone wrong at a corner store.

After that, Stiles was shipped off to foster home number one. It wasn't too bad. The couple were distant but mostly fair, but it didn't take them long to decide they couldn't handle the _inconvenience_ of a grieving teenager and had him sent somewhere else. Foster home number two was much the same, only he stayed there longer—for nearly a year, until he caught one of the other boys trying to force himself on their foster sister and Stiles fought him off. Lies were spun, their foster parents bought them, he got labelled as violent and that was that. Off to foster home number three.

Stiles hated being another statistic. Why couldn't he land in one of the good ones?

Then, at sixteen years old, came home number four, the one he ran away from just a few hours ago. It was the worst of the lot, the couple being religious to the point of fanaticism and also making him attend a religious school. They never allowed him to do anything and made him read the bible for half an hour before bed each night.

Stiles doesn't have much of an opinion on religion—if someone believes and it makes them happy, then great. More power to them.

But that couple? Not in a million years.

The impetus for Stiles' hasty egress was them catching him having his first kiss with another closeted boy behind their school. Oh no, they couldn't have a dirty bisexual under their roof.

They locked him in his austere bedroom without an electronic in sight, and he overheard them whispering right outside, wondering what they should do about him. How to 'help' him with his little 'problem'.

Needless to say, Stiles didn't plan on sticking around to find out their solution. After dinner that night—a tense affair, more so than usual—Stiles managed to sneak back up to his bedroom with a few snacks and a bottle of water from the kitchen, which he stuffed straight in his backpack instead of his school things, along with some extra clothes. Then, in the early hours of the morning, he crept out of his bedroom, thanking his lucky stars that those bastards forgot to lock his door again, and fled into the darkness.

Now, he's here, standing on the side of an empty road far outside of town, waiting for someone to come along and give him a ride to the next one. Maybe farther. He doesn't even have his phone. His feet ache with how long he's been walking, long enough for the sun to have begun its descent. To make matters worse, his water bottle is almost empty and he only has two tasteless protein bars left. If only he could've stolen more, but there was no way he was staying to hoard supplies, risking ending up in some sort of conversion camp or something.

Stiles groans to himself and allows his legs to give out beneath him. He falls hard on his ass and leans back on his arms, his head tilted back, eyes closed. He stays there for a while, as the breeze dries the sweat on his face and he recovers some of his stamina.

He has no idea what the fuck he's going to do. Say he manages to swing a ride from some kind stranger. He gets to the next town and…then what? Just keeps on going? Stays and tries to find a job and somewhere to live? Wherever he worked would have to be someplace shady because he doesn't even have a high school diploma or his GED, so they'd have to pay him under the table.

Is that what his future holds? Nothing but dead-end jobs, loneliness and misery?

Oh, how fun…

He could try to get to NYC and find Scott and his mom, but that would take a long time—and relying on the kindness of strangers that many times seems like a wonderful way to get himself murdered. Why not save them the trouble, then?

Just as Stiles starts contemplating lying there and letting himself die, he hears the rumble of an engine and cracks open his eyes.

A vehicle is coming. By the looks of it, a fancy black sports car.

_Screw it. I'll try one last time…_

Stiles gets tiredly to his feet, walks closer to the side of the road and sticks out his arm, his thumb held up. The car doesn't slow down, so Stiles sighs and braces himself to get a bunch of dust kicked up in his face again. But then, right before the car is about to pass him, the driver decreases its speed and it rolls to a graceful stop, the driver's window right in front of Stiles. The glass is tinted, so all he can see of the person on the other side is a silhouette.

Warily, Stiles approaches and knocks lightly on it. "Uhh…hello?"

The window rolls down and—

Well.

Well, then.

If Stiles wasn't already sure he's bisexual, the man sitting in the driver's seat would have given him one hell of a sexual identity crisis.

"Hey there," the man drawls, resting his elbow on the rim of the open window. His voice is low, gravelly. Sexy, just like the rest of him.

His chiselled jaw is accentuated by salt-and-pepper stubble that matches the hair on his head. His nose is a thin blade, eyes a pretty mix of green and brown with crow's feet at the corners…and that's just his face. From the bare arm Stiles can see—thank you, whoever invented tank tops—he's _ripped_ too. Even the dark hair on his forearm is insanely attractive. If Stiles had to guess, he'd say the man is somewhere in his mid-thirties.

Stiles stands there gaping like a fish out of water. He probably looks like a complete fool, but he can't help himself.

The man quirks a thick eyebrow at him, his lips curling upward into a smirk. His eyes twinkle with amusement. "You looking for a ride?"

"Y-yeah," Stiles stammers. He gives himself a little shake.

"Where to?"

Stiles opens his mouth to say, "Not far," but instead, what comes out is: "However far you're willing to take me."

Stupid.

The other man's smirk turns into a full-blown grin, pearly whites on display. His two front teeth are slightly too long, making him look like a rabbit. Cute. "S'that so?"

"Umm…yes?"

"You don't sound so sure."

Not wanting to take it back and look like even more of an idiot, Stiles doubles down. "I said what I said."

With a nod, the man flicks his eyes to the backpack Stiles left on the ground behind him and then back to Stiles himself. He frowns. "You look pretty young."

Stiles crosses his arms over his chest. "I'm sixteen. So what?"

" _So_ , you in some sort of trouble, kid?"

The concern seems genuine at first glance, and Stiles is tired enough not to look any closer. "Not really," he lies, scuffing his foot against the dirt. He tells the truth immediately afterward, his mouth once more running away from him. "Just homophobic foster parents."

His eyebrows rising on his forehead, the man's expression becomes serious. "Oh."

"That gonna be a problem for you too?"

"Nope. I've sucked a dick or two in my time."

Damnit. Stiles didn't need to know that this man is interested in other men. It puts _ideas_ in his head. "Well…good."

"In that case, sure, I can give you a ride. Grab your stuff and hop in, kid."

Still choosing not to question it, Stiles snatches up his backpack and scurries around to the passenger side of the car. He spots its shiny logo on his way there, which tells him that it's a Chevy Camaro. Pricy. But Stiles already knew it cost a lot.

When he's in the car, the door shut, he stuffs his bag in the footwell and breathes a sigh of relief. He's out of the glare of the sun.

"I'm Derek Hale," the man next to him says, proffering a big hand.

Stiles shakes it and bites back a groan at its warmth and the callouses on his fingers and palm. "Stiles Stilinski."

"Stiles, huh? Interesting name," Derek comments as he pulls up the parking brake.

"It's a nickname." Stiles gets enough of a handle on his mouth this time not to give his real first name.

Time passes slowly after that, the sun still setting. Derek engages him in conversation that starts out surface level, asking Stiles about his favourite foods, bands and everything else under the sun, but soon enough he manages to extract from his passenger a bit more about his past. Stiles talks briefly about Scott, his dad, and how he ended up with the religious psychos he left behind. He's comforted when Derek responds in kind.

Stiles makes all the right sympathetic noises as Derek tells him about the house fire that killed most of his family when he was sixteen—and then about his older sister's death about five years ago.

"That sucks," he says. He curls his hand atop his knee to prevent himself from placing it on Derek's thigh.

The older man shrugs. "It is what it is. I guess you could say we're kindred spirits."

"Yeah…something like that."

To Stiles' disbelief, after they enter the next town and Derek pulls to a stop at a red light, Derek does what Stiles held himself back from doing. Stiles goes rigid in his seat and, against his better judgment, relishes the heat of Derek's hand soaking into his leg. The man removes it again when the light turns green, but only briefly. As soon as he's got the car moving, he drives one-handed and returns his other right back to Stiles' leg, giving him a light squeeze.

Stiles' mind goes blank for the remainder of his time in the car. It's only when he feels the engine cut off that his brain comes back online.

"Is this okay, kid?" Derek asks him, gesturing out the front windshield.

Blinking a few times, Stiles peers at the building in front of them. A motel. Not exactly high-class, but it looks clean enough. Better than all the seedy things he's seen in TV shows and movies, at least.

There's only one problem.

"I don't…I don't have any money," he admits quietly, looking down at his lap. Blood rushes to his cheeks.

"I see." Derek unbuckles his seatbelt and produces a black leather wallet from the pocket of his jeans. From it, he extracts several bills. "Here."

His eyes going wide, Stiles pushes the money away, even as a voice in his head says just to take it. "I can't. I'd feel bad. There's no way I could repay you!"

With a soft hum, Derek stuffs the money back in his wallet. He appraises Stiles closely, and the intensity of his gaze has Stiles shifting in his seat. The air between them becomes charged with tension.

"I could think of a way," Derek says. He swipes his tongue out over his bottom lip.

Stiles doesn't understand. "You can? How?"

"How about I go get us a room for the night, and then…I can collect my payment," Derek suggests.

Oh. _Oh!_

Stiles opens and shuts his mouth several times before he can get his vocal cords to work again. "You mean…?"

Derek winks and gifts him with another smirk. This one is salacious, dripping with promise. "Yes. You're obviously attracted to me, and I'm attracted to you. So…what's it gonna be, kid?"

Stiles can't believe his luck. He managed to find someone who got him away from his foster parents' town, and that person was sexy as hell. Now, that sexy-as-hell man is propositioning him for sex. Part of Stiles feels like a whore for even considering it, but he shuts that part up quickly. This is too good an opportunity to turn down. He gets a free room for the night that's rapidly approaching, somewhere safe and private in which he can rest and finalise a proper plan for the immediate future, and he also gets to lose his virginity to the hottest person to have ever graced the earth.

It's a win-win, in his book. As long as Derek doesn't kill him, but…he doesn't sense any actual ill intent from the man.

Apart from the obvious desire to fuck a sixteen-year-old boy, of course.

Stiles can handle that. "Deal," he says, unbuckling his own seatbelt.

"Great."

Stiles follows Derek out of the car, only just remembering his backpack.

Derek pats his shoulder on his way past. "You wait here. I'll get the room and come back, okay?"

Stiles leans against the side of the Camaro with his backpack dangling from one hand. He surveys the area, mostly people-watching. There's a gas station across the street with a group of boys around his age loitering outside. A couple of them hold lit cigarettes. Further down the street are a few small businesses that have already closed for the day, the windows black and somehow ominous.

Just as the smoking teenagers get particularly rowdy and the person stuck working in the station comes out to shoo them away, Derek reappears.

"Here we go," he says happily, handing Stiles a key. "The room's up on the second floor."

After checking the number for himself, Stiles leads the way to the stairs at one end of the long building. Their room is at the other end of the outside walkway, and after sticking the key in the lock and opening the door, he switches on the light to peruse where he's going to rest his head for the night.

"It's not bad," Derek says as he steps past.

The wallpaper is beige with a dark-brown pattern on it. The carpet is dark, possibly to hide stains, and to the right is a tiny kitchenette with an equally tiny table and two rickety-looking wooden chairs. Beyond that is another door, and a quick peek reveals that it holds a bathroom comprised of just a sink, shower stall and toilet all cramped together. It's reasonably clean. Doesn't even smell.

The most notable part of the motel room itself, though, is the bed right in the middle. Just the one, just large enough for two people to sleep in.

Stiles isn't going to sleep in it for a while.

Anticipation causing his heart to beat faster in his chest, Stiles dumps his backpack on the floor next to the table. "So…what now?" he enquires, unsure how to proceed. "I've never…" He trails off and bites at his bottom lip.

Derek cocks his head to the side. "Never what?"

"Done _this_ before," Stiles admits. His cheeks turn pink. "Y'know…sex?"

Understanding flitting across his rugged yet pretty features, Derek takes a step closer. "Are you a virgin?"

Seriously, Stiles thinks he might pass out, what with how much blood is currently in his face. He's a bit dizzy. "Y-yeah," he admits, breaking eye contact to look at the wall above Derek's shoulder instead.

Said man makes a pleased noise. "I've gotta say, kid, that kinda turns me on."

Blinking, Stiles risks meeting Derek's gaze again. "It does?"

"Knowing I'm gonna be the first one to touch you like that? Oh yeah…it definitely does."

Stiles runs his eyes down Derek's body, and they nearly bug out of their sockets when he gets to the bulge that's growing behind the zipper of his jeans. "Oh…wow."

Coming closer still, Derek doesn't stop until they're chest-to-chest. They're around the same height, but right now, pinned in place by Derek's eyes, Stiles feels tiny. "This must be my lucky day, coming across a treat like you," Derek murmurs, his breath fanning out over Stiles' face. It carries a hint of mint. He reaches up and runs his fingers through Stiles' hair. "Are you gonna be a good boy for me? Let me take your virginity?"

Stiles' own jeans get tighter in the space of a few seconds; he's putting his heart to work today, his blood rushing all sorts of places. "I…"

Derek brushes the back of his hand down the side of Stiles' face. "I think you are. You want it, don't you? Needy little slut like you…you want to be good for me."

And now Stiles is fully hard. What the hell?

He never would've thought that someone speaking to him like this would turn him on. And yet, here he is. Maybe it's just because the degrading words are coming from Derek. From anyone else, they'd probably send him running in the other direction. At least that's the excuse Stiles uses to make himself feel better.

"Answer Daddy, baby," Derek says, his voice sterner.

Stiles chokes on his own breath.

_Daddy?_

"Mmm, you like that don't you?" Derek goes on, interpreting Stiles' shock as arousal. Is he mistaken? Stiles can't say. "It's been a long time since I've had a pretty thing like you. You gonna be Daddy's good boy for the night?"

Stiles hasn't called anyone Daddy in seven years, since he was nine years old, decided it was childish and referred to his father as 'Dad' instead.

No. He shouldn't be thinking of his dad at a time like this. His dad has no place here. This is just between him and Derek.

Derek…who's asking him to call him something Stiles has never thought to call another man again, least of all in this context. He'd be lying if he claimed he wasn't curious. His dick doesn't seem to have a problem with it, twitching and leaking in the confines of his boxer-briefs. The word comes with certain connotations, expectations. It would be nice to relax and just let someone else tell him what to do for a while, let someone else take care of him. No one's taken care of him since he became an orphan, and honestly, he's exhausted down to his bones.

Plus, sexytimes.

"Well? What's it gonna be, baby boy?" Derek asks, gripping Stiles' chin tightly. "Yes or no?"

Stiles figures the room's already paid for—and what has he got to lose? Who knows? He might end up loving it.

Only one way to find out…

Before he can lose his nerve, Stiles squares his shoulders, looks Derek straight in the eye and opens his mouth. "Yes… _Daddy_ ," he says, his voice all high and breathy.

Derek groans in response. "God, baby, that's so good, hearing you call me that," he says, his pupils dilating.

 _That wasn't so bad,_ Stiles muses. He could get used to it.

A second later, Derek crashes their mouths together, and Stiles nearly loses all capacity for thought. This is nothing like the fumbling kiss that got him outed. It's superior in every way. He doesn't know what to do with himself, where to put his hands, and when he attempts to copy what Derek does to him, he just feels awkward. In the end, he puts his hands on Derek's firm chest and lets the older man take charge, guide him, use him however he wants.

Derek's mouth tastes of the mint Stiles smelt earlier, but underneath that, there's something Stiles guesses belongs to Derek himself.

It's nice.

Derek's tongue sliding against his has Stiles' legs growing weak. The older man cups his face in his hands, and it's grounding in a way, keeps Stiles centred in the moment so he can thoroughly enjoy it. Derek's stubble scratches across his own smooth cheeks, adding an element of roughness that serves as the perfect reminder than this is a _man_ he's kissing. It's exhilarating, like a middle finger to those bigots he left behind.

 _Fuck you,_ he thinks righteously, hoping they can somehow hear him. _This is what I want, and you get no say in it, you shit stains._

By the time Derek breaks the kiss, Stiles is breathless and feels kind of like he's flying. "Wow," he says.

"Oh, that's nothing, baby boy," Derek promises, rubbing his thumbs back and forth over Stiles' cheekbones. "Just you wait. When I'm done with you, you'll be ruined for anyone else."

Stiles can't stop a whimper from slipping out.

"Now, let's get this show on the road, hmm?"

The next thing he knows, Stiles is on his knees in front of Derek, Derek's hands pressing down on his shoulders.

"Take me out, kid," the man commands. "Wanna fuck that pretty mouth of yours."

Powerless to do anything but obey, Stiles unfastens the button of Derek's jeans and tugs down the zipper. Derek kicks off his shoes, and then Stiles pulls the garment down his legs and off. He casts the jeans aside and goes to do the same thing with Derek's underwear—black boxers so tight, they leave nothing to the imagination—but Derek stops him.

"Not so fast," he says sharply. "Get nice and familiar with it first."

Stiles' brow furrows with confusion. He looks up at Derek, and when all Derek does is look expectantly right back at him, he does the first thing he can think of. He presses his face against the considerable bulge hidden by Derek's boxers and breathes in automatically. He gets a whiff of something strong and musky, distinctly masculine and far more arousing than it has any right to be. He nuzzles against the length of Derek's dick, marvelling at how thick it is. He can't wait to see it in the flesh.

"That's it, baby. You like the smell of Daddy's cock?" Derek says, fisting a hand in Stiles' hair and tugging.

"Mmhmm." Stiles licks at the tip, where the fabric is damp, and gets a faint taste of Derek's pre-come.

"Say it."

Stiles complies. "I love it, Daddy," he says, the title rolling more easily off of his tongue this time. "Smells so good."

"I'll bet. I've been driving all day, haven't had a chance to shower since last night."

The mere thought should be gross to Stiles, but it's not. He's apparently a hell of a lot kinkier than he initially thought.

Once Derek has had enough and orders him to move on, Stiles yanks down his boxers, wanting to get him naked already. The elastic waistband snags on his dick, but the problem is remedied by Stiles stretching it wide. He nearly gets smacked in the face as Derek's erection is freed, and the boxers fall the rest of the way down Derek's legs on their own. The older man steps out of them and kicks them in the same direction as his jeans before placing his feet shoulder-width apart, his hands loose at his sides. He lets Stiles stare.

And stare Stiles does.

"Oh my God…" he says under his breath.

Right in front of him is another dude's hard dick. He's seen other guys naked in real life before, in locker rooms and such, but this…fuck, it's even better than he could've imagined. Especially because Derek's packing enough to rival most of the men he's seen in porn. Maybe he'd even beat them.

Derek chuckles above him. "See something you like, kid?"

Stiles gives a slow nod. He doesn't look away from Derek's cock for even a second. What is it, eight, nine inches? Beer-can thick too. Damn.

"Why don't you touch it, then? If you're good, maybe I'll let you come tonight."

Stiles wraps a shaking hand around the base of Derek's cock, his pinky finger brushing through dark curls. He gives it an unsure stroke, amazed both by the way his fingers don't reach his thumb and that Derek is uncut. He has foreskin. _Foreskin_.

Stiles himself has none. It's never bothered him—it's just how his dick is—but now, as he strokes Derek's length again, he feels jealous. He loves the way the skin conceals the tip on every upstroke, how it gets all wrinkled and yet soft-looking, and how it peels back to reveal the fat head on every downstroke. Just having a hard cock in his hand that's not his own is a novel sensation too. Stiles enjoys the silky skin and the steel-like hardness beneath, how hot Derek feels in his grip.

"Get your mouth on there, baby," Derek suggests. "Lick over the head. Taste me."

Keeping his hand around the base of Derek's cock so the tip is revealed, Stiles sticks out his tongue and licks right over the slit, where a bead of pre-come was forming. His eyelids flutter and a moan escapes as the taste hits him, so much better now that it's not tainted by the dullness of cotton fabric.

He gives it another few licks and then, feeling brave, takes the head past his lips. He swirls his tongue in circles around it, and at Derek's urging, wiggles it right against the glans on the underside.

" _Ah_! That's it…good boy, making Daddy feel good like this," Derek praises, scratching his short nails lightly over Stiles' scalp.

The praise is all Stiles needs to take more in his mouth. He tentatively bobs his head up and down while stroking over the remaining inches with his hand, getting a feel for it. It's strange having something heavy on his tongue like this, but since he's always had something of an oral fixation, it doesn't take that much time for him to get used to it. He decides he likes it, especially after he gets the hang of keeping his teeth out of play and Derek says again that he's doing well. The praise lights him up inside. It could be dangerous, but he knows without question that he'd do anything to keep Derek heaping praise onto him like that.

"My turn," Derek says a minute later. He tightens his fingers in Stiles' hair, effectively holding him in place.

Stiles can do nothing but kneel there as Derek begins shallowly thrusting in and out of his mouth. Initially, he doesn't go any further than Stiles has already taken him, but then, without warning, he thrusts in deeper, feeding Stiles more of his cock. The boy chokes and gags, his eyes filling with tears as he smacks at Derek's thighs.

It's pointless, though. Derek is immovable, until Stiles' vision goes foggy around the edges and he's seconds away from passing out.

That's when Derek takes mercy on him. He pulls out all the way and grants him a moment to recover, his breaths sharp and ragged as he refills his aching lungs with fresh oxygen, but then he drags Stiles' mouth right back on his dick. Stiles clutches at Derek's muscular thighs and looks up at Derek's face as he's thoroughly used.

The sounds they make together are obscene—Derek's moans, Stiles' choking, and the slick sounds of Derek fucking Stiles' mouth for all he's worth, his heavy balls smacking into Stiles' chin. It creates a cacophony of filth, and with the part of Stiles' brain that's not filled with _air, air, need air, need to breathe, fuck,_ he feels sorry for whoever's in the motel room next to theirs. It must be obvious what's happening.

"Mmm…there's a good boy," Derek grits out, tipping his head back. "This is where you belong, isn't it? Down on your knees, begging to be used. Daddy's little whore!"

Derek's thrusts get even rougher, uncoordinated, before he leaves Stiles' mouth altogether. He continues to hold him in place with the hand in his hair, while using the other to jerk himself off in front of Stiles' face.

"Stick out your tongue," Derek orders, his chest heaving.

Stiles does so just in time. He watches as Derek's orgasm wracks through him, the muscles of his arms bulging, toes curling in the carpet as he shoots onto Stiles' waiting tongue. There's so much that some of it drips down Stiles' chin and onto his chest, staining his T-shirt, but he's filled with too much awe to care.

 _He_ did this. He made a man as hot as Derek Hale come.

Honestly, he's kind of proud of himself.

Once his orgasm ends, Derek releases his softening cock, opens his eyes and looks down at Stiles with an expression that's almost fond. "Look at you," he says with a grin. "Covered in my come… S'it nice, baby?"

Stiles retracts his tongue and swirls the jizz that landed on it around his mouth. It's better than Derek's pre-come, and _way_ better than the time Stiles felt a bit adventurous and tasted his own load after a late-night masturbatory session a couple years ago. He hums his approval and swallows it while staring right into Derek's eyes, ensuring he sees his throat work.

Derek chuckles. "That's what I thought." He ruffles Stiles' hair. "You're just a dirty little cumslut, aren't you?"

After using a finger to feed Stiles the come that dripped down his chin, Derek grabs him under his arms and, in a display of great strength, tosses him effortlessly onto the bed. Stiles bounces a few times atop the mattress before coming to a stop. He leans up on his elbows and waits for whatever Derek has planned for him next.

"Luckily for you," the man says, approaching the bed too, "I'm not so old that I can only come once—and with a pretty slut like you, baby boy, I can _definitely_ get hard again."

As a form of proof, Derek's cock never goes fully soft. It swings back and forth between his thighs with each step.

When he reaches the bed, Derek peels his tank top up his torso, giving Stiles his first view of him fully naked. Boy, was it worth the wait.

Derek is six feet of muscle, tanned skin and hair.

His pecs are so big they're like tits, his nipples pebbled and suckable. They're covered in a field of dark hair that Stiles would really like to run his fingers through. This hair tapers into a long line down the centre of his abs, past his bellybutton to join his pubes—and that's not all.

Derek, apparently enjoying being the sole object of Stiles' attention, gives him a cocky grin and does a slow 360-degree turn.

Derek's back is equally toned, the muscles shifting beneath his skin, and in the middle of his shoulder blades he has a black tattoo of three spirals that meet in the middle. Stiles thinks he's seen it before but can't remember its name. Lastly, lower down, Derek's ass is tight and perfectly plump. It sports yet more hair, more abundant closer to the crack. Stiles wants to stick his face right in there.

"Your turn, kid," Derek says when he's completed his turn.

He kneels on the bed, drags Stiles closer to the edge and strips him out of his clothes. Stiles lets him, raising his hips so he can take off his jeans and underwear, and then his arms so he can take off his T-shirt.

"Beautiful," Derek compliments once the floor is decorated with both of their clothes.

Stiles ducks his head, bashful. "Thanks…"

"Thanks, what?" Derek prompts.

Stiles lies there, bemused, but swiftly remembers and corrects himself. "Thanks, Daddy."

"That's better. You're welcome, baby boy." Derek forces Stiles' legs open and insinuates himself between them. "I'm gonna have fun defiling you."

Stiles gasps when Derek takes his cock in hand. Unlike the older man, he's average at best, but as Derek strokes him, he actually looks _small_ —and he's not the only one to notice.

"Such a pretty dick," Derek says with a cruel laugh. "So small and cute."

It's humiliating, emasculating—and Stiles loves it. Yet another kink to add to his ever-growing list.

He bucks up into Derek's grip, his cock aching with the need to come, but Derek releases him, denying it.

" _Ah-ah_! Not yet," the man says. "Not until I'm inside you. Flip over, get on your hands and knees."

Blushing all over again, Stiles gets into the requested position, his heart beating faster because it's so vulnerable. The sensation of being exposed gets worse when Derek does nothing behind him, doesn't move, doesn't speak…just kneels there. Stiles can feel his eyes on him and gets the urge to hide himself, but he doesn't follow through. The desire not to disappoint Derek keeps him in place, even when Derek finally does _something_ , pressing a dry thumb against Stiles' asshole.

"So tight," Derek whispers reverently. "You really are a virgin, aren't you?"

Stiles whimpers. "Daddy…"

"I just might have to take a picture when I'm done with you, so you can see how gaping and wrecked I'm gonna leave you."

Another whimper. The thought of letting Derek take a photograph of him…

Before Stiles can figure out how he feels about that, Derek puts his mouth on him and he forgets about it. He tangles his fingers in the bedsheets as Derek runs his tongue in circles around his hole, getting him wet, coaxing him to loosen, to open up ready for his prodigious cock.

The first time the tip of Derek's tongue breaches him, Stiles falls from his hands and the side of his face ends up smushed into the bedding. His ass remains raised, though, his back becoming a sinuous arch and his hole better presented for Derek—for _Daddy_. Fuck, thinking that word has the pleasure of being rimmed ratcheting up higher, the hairs on his arms standing on end. Maybe it's just because he's too turned on to feel awkward about it anymore, but it didn't take long at all for calling Derek by that name to seem less like he's playing a role and more…natural.

Now, he's fully on board with it. He almost forgets the reason he and Derek are here in the first place. It no longer seems like it's so Stiles has a roof over his head tonight, but because he wants it. Nothing else matters. Everything else—the shit in his past, the religious nutjobs he fled from—it's all faded away like it was never important. All that exists right now is what's inside the motel room.

All that matters is getting Daddy's dick inside him, pronto.

"Daddy!" Stiles exclaims, shoving his ass back onto Derek's tongue. "So good…"

Derek squeezes Stiles' ass cheeks, seals his lips around his rim and, with the tip of his tongue still inside the boy, _sucks_.

The noise Stiles makes…he's never made it before. It's a wail, loud and desperate. His cock leaks pre-come where it hangs underneath him, his balls drawn up tight. If he could just get a tiny bit of stimulation, it would be over.

Derek does the sucking thing a few more times, while growling sounds emanate from deep within his chest. They conjure the image of an apex predator playing with his food. And then, with a final lick over Stiles' rim, he removes his mouth and replaces it with one of his fingers. He doesn't ease it in, but slides it in all the way up to the last knuckle.

"Gonna get you stretched out for me," he says, bringing his other hand down on Stiles' ass cheek.

The bright spark of pain has Stiles yelping and his hole clenching down tight around Derek's finger.

"You'd look amazing with your ass all pink, wearing my handprints," Derek goes on, his voice still carrying that animalistic growl. "But, for now…"

He gives Stiles a second spank, on the other cheek this time, before concentrating on working Stiles' body open for his dick. Stiles hides his face in his crossed forearms as a second finger invades him and Derek scissors them apart. There's a distinct burn to it now, but his erection never flags because he knows exactly where this is heading. The thought of getting fucked by Derek's huge cock is both daunting and exciting. He chose a hell of a guy with whom to have his first time. Could've started out with a pencil-dick, but _no_ …he went with the guy with the baseball bat between his legs.

A third finger has Stiles hissing through his teeth; spit really isn't an adequate substitute for lube.

Derek smooths his palm down Stiles' back. "Shh…almost there."

He spits on Stiles' hole to make things easier, and when he's able to wedge his pinky finger in alongside the other three, he deems Stiles ready for him.

Using a mixture of yet more spit and his own pre-come, Derek slicks up his renewed erection and drapes himself over Stiles' back, his cock slotting between Stiles' cheeks. He thrusts lazily a few times, teasing the boy a little, before using one hand to aim the tip at the boy's prepped hole. He plants the other next to Stiles' head, keeping most of his weight off of him so as to not crush him.

"Ready, kid?" he enquires, nibbling on Stiles' earlobe.

Turning his head, Stiles catches Derek's mouth in another kiss. This one feels less like a claim and more calming, reassuring.

"Do it, Daddy," Stiles says against Derek's mouth. "Want your cock."

"I know you do," Derek replies with a smirk. He licks the taste of Stiles off of his lips. "You're such a needy slut."

The first push forward is tough. Stiles' hole, even with four fingers' worth of prep, is still tight enough that he struggles to accept Derek's fat cock. But Derek is unrelenting. He pushes and pushes and then pushes some more, even as Stiles sucks in a sharp breath of pain, until the head pops past the first ring of muscle. Even then, he doesn't cease. He keeps going, forcing inch after inch into Stiles' virgin body. He grips Stiles' hips to hold him in place, his grip so tight that he'll probably leave bruises behind. All Stiles can do is grin and bear it, his hole being pushed to its limits.

When, finally, all nine inches are sheathed, Derek lays himself fully over the boy's back. Stiles' knees slide out from beneath him as Derek presses him down into the mattress with all two hundred pounds of himself. His dick, softer now, ends up trapped between his stomach and the bedsheets. Derek's weight is nice. It distracts Stiles enough that the bright burning in his poor hole lessens, banished to the back of his mind where it's not as noticeable.

"Fuck, you feel _amazing_ , kid," Derek mumbles, his breath blowing out hot over the shell of Stiles' ear. "So warm and tight…all mine."

Stiles grunts and concentrates on the press of muscle against his back. It doesn't get much better for what feels like an hour, but then his body acclimates to being filled to the brim and the burn lessens to nearly nonexistent. Derek must be able to tell—maybe from how Stiles loosens slightly around him—because he levers himself up on his arms, hands on either side of Stiles' head, and begins withdrawing. He leaves Stiles feeling hollowed out, and as hard as it was to take the first time, he finds himself missing Derek's cock when it's gone.

Fortunately for him, it's back again a second later. Derek's first few thrusts are syrupy slow, the drag of his cock pleasant in its own way, stimulating nerve endings in Stiles' hole that he never knew existed. Each time he pulls out, Stiles can feel himself clinging to the thick length, like he's trying to suck Derek back inside.

Almost like Derek belongs there.

Then, with his next thrust, the man adjusts the angle and the head of his cock brushes against something inside Stiles that sends lightning shooting up his spine. He cries out, and it takes a moment for him to recall what it is.

His prostate—or the male G-spot, as he read it referred to in a bout of late-night research last year.

"There it is," Derek says above him, his amusement evident in his voice. He aims for it again, and again, Stiles' body lights up from the inside. Blood rushes back to his dick.

"Daddy!"

Derek growls. He moves one of his hands to the back of Stiles' neck, gripping it tightly, pinning him down. "That's it…just give in to it…"

As if Stiles has any other choice now.

He scrabbles at the sheets as Derek kicks things up a notch, fucking Stiles faster, harder, their skin slapping together. He tugs at the material and thinks he hears something rip, but he doesn't have the brain capacity right now to give it more than a brief thought of, "Oops." Then he's lost again to how awesome it feels to get pounded into the mattress like this. Derek's heavy balls smack into Stiles' every time he fucks all the way back inside, adding a touch of pain that only heightens the pleasure.

Throughout all of this, Stiles' cock, once more fully erect, remains trapped. It's sore now, and the underside rubbing against the slightly rough fabric of the sheets doesn't help. The way is slicked slightly by the buckets of pre-come Derek is forcing out of the slit by hitting his prostate every few thrusts, but it still rides the edge, pleasure threatening to turn into overstimulation. He goes to wedge a hand beneath himself to provide something better to rut against, but Derek stops him.

"Oh no you don't!" the man growls. He picks himself up and brings Stiles with him so they're both kneeling on the bed. He grips both of Stiles' wrists in one big hand and curls the other around the front of Stiles' neck, not cutting off his air supply but exerting just enough pressure for him to feel it. "You're not coming at all unless it's on my cock!"

"Da—" Stiles chokes out, clenching and unclenching his hands. He's helpless. "Daddy! _Please_!" he begs.

"I'm not— Stopping you," Derek says between thrusts. "You can come anytime. It'll just— Have to be untouched. Like the whore— You are."

Stiles releases that wailing sound again. It's humiliating, which, oddly enough, makes it awesome.

Derek is so rough with him now, jackhammering his cock into Stiles' hole, that the headboard slams into the wall, giving their neighbours more evidence of their lewd activities. Stiles wouldn't be shocked if they got a noise complaint by the time they're done.

His cock bounces wildly with each of Derek's thrusts, pre-come flying everywhere from the tip. He's nearly there again, craving just a touch to get him off, but Derek's hand around his wrists is inexorable. It just goes on and on, his body sweating even though he isn't doing any of the work, the headboard slamming, that tingling in his lower gut sparking more and more but never actually catching fire. Tears appear in his eyes. He blinks them back but they just keep coming, soon spilling over.

"Aww, baby boy, something wrong?" Derek coos at him, tightening his hand around Stiles' neck.

"D-Daddy," Stiles croaks. "Please…"

"You can do it," the man encourages. "You've been so good so far tonight. A whore like you? I know you can come untouched for me."

It hurts now. Stiles' feet are right at the edge of the cliff but he's unable to actually throw himself off. With a sob, he shakes his head as best he can, more tears leaving tracks down his cheeks.

It's enough for Derek to take pity on him. He releases Stiles' neck and slides his hand down the front of his body, all while fucking him like a beast. He reaches Stiles' cock, nearly purple now, but doesn't wrap his hand around it to give the boy something to fuck. His touch is light, barely there, like a feather whispering over skin.

But it's enough. It's _just_ enough.

Stiles throws his head back and screams hoarsely as he goes off like a rocket, jizz spurting from him to spray across the bedding. His orgasm is prolonged by Derek still hitting his prostate every few seconds, and by the time it's done, Stiles thinks he might have passed out for a moment or two. One second, Derek holds him up and continues to destroy his hole, and the next, he finds himself lying face-down on the bed with Derek's weight back on top of him. The man is unmoving, breathing shakily into the side of Stiles' neck, sweat sticking them together.

Derek's cock is still inside him, hard, but Stiles can feel it getting softer. He's both sated and disappointed that it's over.

For another few minutes, they lie there quietly as they recover. Stiles can't quite get enough air into his lungs with Derek atop him, but he can't seem to gather the wherewithal to offer up a complaint. He just has to deal with it until Derek rolls off to the side. He lies on his back with an arm thrown above his head and the other draped over his own stomach. His cock is flaccid and sticky with his own release where it rests against his hairy thigh.

As for Stiles, Derek wasn't wrong. He feels _ruined_ , his hole unable to tighten back up all the way.

Derek breaks the silence. "Well, that was definitely worth the money," he says, turning his head to the side to look at Stiles.

Stiles can only blink blearily back at him.

With a short huff of laughter, Derek sits up and situates himself behind Stiles, using his hands to spread Stiles' cheeks. "Let's see how you look… _yeah_ , that's just what I wanted," he says approvingly.

Stiles manages to speak, but only one word. "Daddy…"

"I know, kid." Derek rubs a finger around Stiles' rim. "You must be sore, huh? My come's dripping outta you, and you're gaping so much, I can see your pretty pink insides."

Stiles shudders. His cock twitches valiantly beneath him, but he's far too worn out to get hard again.

His eyes shutting of their own volition, Stiles barely feels it as Derek leaves the bed. He can hear the man puttering around the motel room, but it gets more and more difficult to pay attention. Eventually, even the sounds get fainter, and the last thing he registers before he falls asleep is another sheet being tucked around him.

* * *

Later, when Stiles wakes up again, the first thing he sees is the clock on the bedside table. 8:22 a.m. He slept through the whole night. Stretching, he turns over and sits up, wincing as his hole twinges with pain. Then he winces for an entirely different reason.

A much worse one:

Daddy—no, _Derek_ —is gone. The only proof that he was ever there is the state of the bed and Stiles himself, both sticky and dishevelled.

"Oh…" Stiles says to the empty motel room.

He didn't expect Derek to stay, but…somehow, he's still crestfallen.

He sits there for a while longer, attempting to push the feeling away and not drown under the weight of reality setting in again. His future is still uncertain, and he doesn't know what he's going to do about it.

When he feels as good as he's going to, he shuffles to the side of the bed and stands, ignoring the wetness that drips down the back of his thigh. He rummages around in his backpack for a fresh set of clothes and prays that this motel has some decent toiletries in the bathroom. Just as he's about to head in there and switch on the shower, also praying for decent water pressure, he hears a knock on the door. It's probably the owner of the motel coming to tell him it's time to check out or something.

Stiles hastily puts on the clothes Derek ripped off of him last night. "Just a minute!" he calls, nearly tripping over as he sticks his legs in his jeans.

Once his modesty is covered, Stiles opens the door. His breath flees his lungs because it's not a stranger on the other side.

"Good, you're still here," Derek says, scratching at the back of his neck. Unlike Stiles, he's in clean clothes—a maroon henley, black jeans and a well-loved leather jacket. "I didn't know if you would be."

Because he's a dumbass, Stiles' responds with, "What're you doing here?" as if he didn't miss Derek as soon as he realised he was gone.

Lowering his hand, Derek's countenance is earnest but uncomfortable. "I felt bad about just taking off like I did."

Stiles nods dumbly. "Okay?"

Glancing behind himself, like he's checking that there's no one else close by, Derek sticks his hands in the pockets of his leather jacket and rocks back on his heels. This body language is a big contrast to the cocksure, domineering demeanour he displayed during their time together yesterday. "I was wondering something…"

"Okay," Stiles repeats.

"You have nowhere to go, right?"

With a frown, Stiles shakes his head. "No."

"Then come with me," Derek blurts out, surprising them both.

Stiles' mouth hangs open like it did when they first met. "W-what?"

"You should come with me," Derek says, doing that rocking motion again. "You have nowhere to go, I enjoyed our time together last night, and where I'm headed is far away from your foster parents."

Stiles' first instinct is to say yes—it's a solution, potentially an excellent one—but he keeps the word back. "Where are you going?" he queries instead.

"After the fire, Laura and I moved to New York—the city, specifically," Derek explains. "I was in California for business, and I was headed back home when I picked you up. You could…come with me. I've got an apartment there. You could stay in my guest room—or I could help you find your own place, if you'd prefer that."

Stiles grips the doorframe as relief overwhelms him. It sounds too good to be true, which means it probably is. But hey, the voice in the back of his head told him that getting picked up and propositioned by Derek was too good to be true as well, and that turned out alright in the end. He still doesn't get a bad vibe off of Derek, and he really doesn't have any plans or ideas for what he can do to make his way through the next few months. Hell, he wouldn't even know what to do _today_.

Plus, Derek said he was going to NYC. Scott's in NYC.

Stiles doesn't believe in fate or destiny or anything hokey like that, but Derek's offer makes a good case for it.

"Okay," he says, fighting the desire to leap into Derek's arms like he's his personal knight in shining armour.

Derek's mouth stretches into a grin that's unlike the others Stiles has seen from him. It's just…happy. Huh.

"Okay…" the man echoes, taking his hands out of his pockets. "Okay, that's good."

Stiles finds himself smiling too. "I was just gonna take a shower, but…we can leave afterward. If that works."

"It works. Trust me, it works." Derek follows him back into the motel room and takes a seat at the table next to the kitchenette. "I'll be out here."

Stiles nods, grabs his clean clothes from where he dumped them on the foot of the bed and ventures into the bathroom. He gets a last glimpse of Derek at the table before he shuts the door. The smile is still on Derek's face.

In semi-privacy now, Stiles leans back against the door and sighs, clutching his clothes to his chest.

He still doesn't know for sure what's to come. This thing—whatever it is—with Derek could not work out, leaving Stiles stranded and on his own again. But, for now, Stiles chooses not to look a gift horse in the mouth. He'll roll with the punches, accompany Derek to NYC and see what happens.

His future's looking up.

**Author's Note:**

> Well, this took much more time to write than my past few PWPs, but I think it was worth it. It turned out a bit longer too. While Derek maybe came off a bit creepy at the start—what with propositioning a sixteen-year-old boy in a desperate situation and all—I couldn't resist ending this PWP on a sweet, hopeful note. I don't plan on writing a continuation, but I like to believe that they lived happily ever after. Please let me know what you thought.
> 
> Thank you to Lazydink for giving me this prompt. I hope it was everything you wanted it to be. :)
> 
> Stay tuned for my next PWP, in which Derek initiates his first time with Stiles in the middle of a puppy pile, saying that it needs to be this way for him to become a proper part of the pack. No one else will actually participate. They'll just watch (and marvel).
> 
> **P.S. Don't forget to subscribe to me to be notified when my future updates go live. And please check out my past fics if you haven't already and are interested.**


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